The Journal of Organic Chemistry 2018-04-06

Cu-Mediated Sulfonyl Radical-Enabled 5-exo-trig Cyclization of Alkenyl Aldehydes: Access to Sulfonylmethyl 1H-Indenes

Jiabin Ni, Yu Xue, Liping Sun, Ao Zhang

Index: 10.1021/acs.joc.8b00341

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Abstract

An efficient method for the construction of sulfonylmethyl 1H-indenes via Cu(I)-mediated sulfonyl radical-enabled 5-exo-trig cyclization of alkenyl aldehydes has been developed for the first time. Mechanistic studies indicated that a radical addition–cyclization–elimination (RACE) process might be involved. The reaction features a relatively broad substrate scope, good annulation efficiency, and varying functional group tolerance.